1. Field of the Invention
The present invention relates to a complex composed of cucurbituril and fullerene and a method for manufacturing the complex on a solid-phase.
2. Description of the Related Art
Cucurbituril contains hard cavities, and thus it can be properly used as a host for small organic compounds. In fact, an 1:1 complex or an 1:2 complex of cucurbit[6]uril (or cucurbit[7]uril) and a guest material has been introduced, and concretely a complex of cucurbit[7]uril and 4,4′-bipyridinium-dication, produced in an aqueous solution containing alkaline-metal salt, has been reported (Mock, W. L. and Shih, N. -Y., J. Org. Chem. 1986, 51, 4440; Ong, W. et al., Org. Lett. 2002 4, 1791; and Kim, H. -J. et al., PNAS 2002, 99, 5007). Different from cyclodextrin, a carbonyl group, located at the entrance of a cavity of cucurbituril, can be coupled with polarizable molecules and ions by ion-bipolar reaction and/or hydrogen bonding (Mock, W. L., Top. Curr. Chem. 1995, 175, 1; and Cintas, P. J., J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 17, 205). These complexes are generally produced in a solution, or produced by two-phase reaction between solid-phase cucurbituril and liquid- or gas-phase guest molecules (Mock, W. L. and Shih, N. -Y., J. Org. Chem. 1986, 51, 4440; and Buschmann, H. -J. et al., European Water Pollution Control 1996, 6, 21).
Cucurbit[6,7]uril is a very desirable composition unit of an acceptor-supramolecule compound composition (Jeon, Y. -M. et al., J. Am. Chem. Soc. 1996, 118, 9790; and Zhao, J. et al., Angew. Chem. Int. Ed. 2001, 40, 4233), however, its characteristics and applicability have not been studied very much. Up to the present, guest materials that have been used for manufacturing a cucurbituril-containing complex are limited to iodine (Saenger, W., Angew. Chem. 1980, 92, 343), dyes for water-purification (Buschmann, H. -J. et al., European Water Pollution Control, 1996, 6, 21), and alkyl-and aryl-ammonium ions (Mock, W. L.; Shih, N. -Y.; J. Org. Chem. 1986, 51, 4440). And, it has not been reported about a complex of cucurbituril and nonpolar guest material.
In addition, fullerene has a very high reactivity to a free radical (Krusic, P. J. et al., Science 1991, 254 1183; Geckeler, K. E. and Arsalani, N., Fullerene Sci. Technol. 1996, 4, 897; and Ford, W. T. et al., Macromolecules 1997, 30, 6422) and is able to cut DNA with light being existed, and thus it has very high applicability for bio-medicines. Consequently, it has been broadly researched on a host-guest material chemistry of [60]fullerene. It has been reported that various molecules such as β- and γ-cyclodextrin' (Murthy, C. N. and Geckeler, K. E., Chem. Commun. 2001, 1194; Murthy, C. N. and Geckeler, K. E., Full., Nanotubes, & Carb. Nanostructures 2002, 10(2), 91; and Anderson, T. et al., Chem. Soc. Chem. Commun. 1992, 604), calix[3,5,6,8]arenes (Ikeda, A. et al., J. Am. Chem. Soc. 1999, 121, 4296; and EP0686644), and porphyrin-metal macro-ring (Tashiro, K. et al., J. Am. Chem. Soc. 1999, 121, 9477) are working as a host for [60]fullerene respectively.